Chirality in natural and applied science:
Gespeichert in:
| Format: | Buch |
|---|---|
| Sprache: | English |
| Veröffentlicht: |
Oxford
Blackwell Science [u.a.]
2002
|
| Ausgabe: | 1. publ. |
| Schlagworte: | |
| Online-Zugang: | Inhaltsverzeichnis |
| Beschreibung: | XIII, 313, [4] S. Ill., graph. Dars. |
| ISBN: | 0632054352 0849324343 |
Internformat
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| 245 | 1 | 0 | |a Chirality in natural and applied science |c ed. by W. J. Lough ... |
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Datensatz im Suchindex
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|---|---|
| adam_text | Titel: Chirality in natural and applied science
Autor: Lough, W. John
Jahr: 2002
Contents
Contributors
Introduction—retournons Pasteur!
K. MISLOW
References
1 Pasteur on molecular handedness—and the sequel
S.F. MASON
Pasteur s optical resolutions
The chemical-physics background to Pasteur s 1848 discovery
Molecular structure theory and stereoselective chiral synthesis
Chance, necessity, and chiral fields in the evolution of biomolecular
homochirality
Parity and its non-conservation
References
2 The origin of biomolecular chirality
A.J. MACDERMOTT
Introduction
Homochirality—a hallmark of life
Homochirality—also a pre-condition for life?
The need for a chiral influence
False chirality—magnetic fields
True chirality—circularly polarized photons
True chirality—the w boson
True chirality—the z boson
Amplification mechanisms
PVEDS of biomolecules
So was it really the weak force?
Look in space!
Is the universe intrinsically handed?
References
3 Chirality at the sub-molecular level: true and false chiralitv
L.D. BARRON J
Introduction
Symmetry principles
i
iii
vii
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3
11
15
17
19
23
23
23
24
24
28
29
31
33
35
37
41
42
46
49
53
53
56
viii
Non-observables and symmetry operations 56
Symmetry of physical quantities 57
Symmetry in quantum mechanics 58
Parity 58
Time reversal 59
Charge conjugation 60
True chirality 61
Natural and magnetic optical activity 61
A new definition of chirality 62
Translating spinning electrons, photons and cones 63
Electric, magnetic and gravitational fields 64
Absolute asymmetric synthesis 65
Truly chiral influences 66
Falsely chiral influences 66
The breakdown of microscopic reversibility induced by a
falsely chiral influence: enantiomeric detailed balancing 67
Unitarity and thermodynamic equilibrium 69
Chirality and symmetry violation 70
The fall of parity 70
Parity violation in atoms and molecules: true enantiomers 72
Violation of time reversal and CP violation 74
CP violation is analogous to chemical catalysis! 75
CPT violation 75
The mixed-parity states of a chiral molecule 76
The double well model 76
Two-state systems and parity violation 78
Parity violation and spontaneous parity breaking 80
Chirality and relativity 81
Chirality in two dimensions 82
Concluding remarks 83
Acknowledgements 84
References 84
4 The molecular basis of chiral recognition 87
J. GREER and I.W. WAINER
Introduction 87
Kinetic and thermodynamic aspects of enzymatic enantioselectivity 88
Kinetics of enzymatic reactions 88
Thermodynamics of enzyme reactions 89
Enzymatic enantioselectivity 89
Molecular chiral recognition mechanisms 91
The three-point model 91
A re-examination of the three-point model 92
Conformationally-driv.en molecular chiral recognition 94
The N-dechloroethylation of ifosfamide enantiomers 94
Interaction of peptides and larger molecules with chiral biopolymers 96
Binding of peptides and peptide-like moieties to a protein 96
How critical are the chiral centres for binding to the enzyme? 101
ix
Modification of multiple centres 1U1
Modification of one centre at a time 103
Concluding remarks ^
References
5 Chirality in drug design and development 109
D.J. TRIGGLE
Introduction 109
The stereoselectivity of drug-receptor interactions 110
Biological consequences of stereoselective drug action 113
The basis of stereoselectivity 116
Absorption U?
Distribution 117
Metabolism 118
Excretion 120
Stereoselectivity of drug classes 120
G protein-coupled receptors: ^-adrenoceptor antagonists 120
Ion-channel receptors: voltage-gated Na+ and Ca2* channels 123
General anaesthetic receptors: general anaesthetics 128
Regulatory requirements for chiral drugs 128
Decision processes 130
Acknowledgements 131
References 131
6 Chirality in medicinal chemistry 139
P.N. PATIL and D.D. MILLER
Historical aspects 139
Stereoselectivity of the biosynthesis of transmitters and related
medicinals 141
Affinity and intrinsic activity 144
Steric aspects of drug action at the cholinergic neuroeffector junction 146
Muscarinic agonists 146
Nicotinic agonists 149
Acetylcholinesterase inhibitors 150
Cholinergic muscarinic blockers 151
Nicotinic cholinergic blockers 153
Steric aspects of drug action at the noradrenergic and dopaminergic
neuroeffector junction j54
Inhibition of noradrenaline transport 155
Chirality at postjunctional receptors 157
Purity of enantiomers 157
Receptor active conformation 158
Conformation induction by enantiomers 160
Efficacy and isomeric activity ratios 161
The Easson-Stedman hypothesis 161
Deviation from Easson-Stedman hypothesis 162
x
Chirality of adrenoceptor blockers
Competitive reversible a-adrenoceptor blockers
Irreversible a-adrenoceptor blockers
Enantiomers of ^-adrenoceptor blockers
Concluding remarks
Acknowledgement
References
7 Separation of chiral compounds—from crystallisation to
chromatography
W.J. LOUGH
Crystallisation
Russia, Israel, and NMR
Derivatisation
Commercialised chiral HPLC
Chiral HPLC beyond the eighties
Beyond HPLC
Meeting unfulfilled needs?
References
8 Electronic circular dichroism—fundamentals, methods and applications
P. SALVADOR!, L. DI BARI, and C. ROSINI
Introduction
Phenomenological aspects
Instrumentation—essential description of a dichrograph
Towards an understanding of optical activity and related phenomena
Preliminary considerations
Macroscopic characteristics of an optically active medium
The helix model
The nature of electronic transitions
Dipolar strength
Rotational strength
Symmetry properties of the rotational strength—spectroscopic
foundation of optical activity
Classification of optically active molecules
Optical activity of dissymmetric chromophores
The independent systems approach
Coupled oscillators
Applications to structural chemistry
Empirical correlations
Semi-empirical rules
Helicity rules
Sector rules
Chirality rules
164
164
167
168
170
171
171
179
179
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183
184
189
192
195
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203
203
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214
214
215
216
216
217
219
220
220
224
224
224
226
xi
Non-empirical methods of analysis 227
Conclusions and future perspectives 233
References 234
9 Chirality in the Natural World: Chemical Communications 241
K. MORI
Introduction 241
When was chirality found to be important in chemical communications? 243
Background—theory of olfaction in the 1960s and early 1970s 243
Pioneering work with insects 243
The bioactivity of pheromones depends on their chirality 244
How was the utmost importance of chirality in chemical
communications recognized? 246
Synergistic response based on enantiomers—sulcatol 246
Inhibition by the wrong enantiomer—disparlure and japonilure 247
One enantiomer is active against males whereas the opposite
enantiomer affects females—olean 247
Chirality plays a role even with an achiral pheromone 248
Current understanding of the importance of chirality in chemical
communications—stereochemistry-bioactivity relationships among
pheromones 249
Only one enantiomer is bioactive, and its antipode does not inhibit
the action of the active stereoisomer 249
Only one enantiomer is bioactive, and its antipode inhibits the
action of the pheromone 249
Only one enantiomer is bioactive, and its diastereomer inhibits the
action of the pheromone 250
The natural pheromone is a single enantiomer, and its antipode or
diastereomer is also active 250
The natural pheromone is an enantiomeric mixture, and both
enantiomers are separately active 251
Different enantiomers or diastereomers are employed by different
species 252
Both enantiomers are necessary for bioactivity 253
One enantiomer is more active than the other stereoisomers), but
an enantiomeric or diastereomeric mixture is more active than that
enantiomer alone 253
One enantiomer is active on males, the other on females 254
Only the meso isomer is active 254
The practical importance of chirality in pheromone-based pest control 255
Conclusion 255
Acknowledgement 255
References 255
10 Chirality in the natural world—odours and tastes 261
W.A. KONIG
Introduction
261
xii
The influence of chirality on biological activity 262
The relationship between olfaction and chemical structure 264
The relationship between odour and taste and chirality 264
Enantiomeric odour differences and their quantitative measurement 265
Analysis of the configuration and enantiomeric composition of
volatile chiral compounds 266
Stereochemical analysis of odorous compounds 267
Monoterpene hydrocarbons 267
Terpene alcohols 270
Carbonyl compounds 273
Sesquiterpenes and related compounds 277
Sulphur compounds 279
Electronic nose , sensor technology 280
Concluding remarks 281
References 281
11 Chirality in the natural world: life through the looking glass 285
C.J. WELCH
Introduction 285
Background 286
Special problems in the study of asymmetric organisms 286
The machinery of life: symmetric organisms from asymmetric
building blocks 289
The asymmetry of microorganisms 291
Asymmetry in the plant world 291
Asymmetry of invertebrates 294
Asymmetry of fishes 296
Asymmetry of birds 297
Asymmetry of reptiles and amphibians 298
Asymmetry of mammals 298
Asymmetry in humans 299
Some recent advances in the developmental biology of animal asymmetry 300
Behavioural asymmetry 300
Summary and conclusion 300
Acknowledgements 301
References 301
Concluding Remarks—Chirality, Chemistry, the Future 303
THE EDITORS
References 304
xiii
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| spelling | Chirality in natural and applied science ed. by W. J. Lough ... 1. publ. Oxford Blackwell Science [u.a.] 2002 XIII, 313, [4] S. Ill., graph. Dars. txt rdacontent n rdamedia nc rdacarrier Chirality Chiralität Chemie (DE-588)4147732-7 gnd rswk-swf Chirale Verbindungen (DE-588)4348527-3 gnd rswk-swf (DE-588)4143413-4 Aufsatzsammlung gnd-content Chirale Verbindungen (DE-588)4348527-3 s DE-604 Chiralität Chemie (DE-588)4147732-7 s Lough, W. John Sonstige oth HBZ Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=009930832&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Chirality in natural and applied science Chirality Chiralität Chemie (DE-588)4147732-7 gnd Chirale Verbindungen (DE-588)4348527-3 gnd |
| subject_GND | (DE-588)4147732-7 (DE-588)4348527-3 (DE-588)4143413-4 |
| title | Chirality in natural and applied science |
| title_auth | Chirality in natural and applied science |
| title_exact_search | Chirality in natural and applied science |
| title_full | Chirality in natural and applied science ed. by W. J. Lough ... |
| title_fullStr | Chirality in natural and applied science ed. by W. J. Lough ... |
| title_full_unstemmed | Chirality in natural and applied science ed. by W. J. Lough ... |
| title_short | Chirality in natural and applied science |
| title_sort | chirality in natural and applied science |
| topic | Chirality Chiralität Chemie (DE-588)4147732-7 gnd Chirale Verbindungen (DE-588)4348527-3 gnd |
| topic_facet | Chirality Chiralität Chemie Chirale Verbindungen Aufsatzsammlung |
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